Yarn conditioning process



Patented Apr. 9, 1940 UNITED STATES 2,196,755 YARN CONDITIONING PROCESSJoseph B. Dickey, Rochester, N. Y., assignor to Eastman Kodak Company,Rochester, N. Y., a corporation of New Jersey No Drawing. ApplicationDecember 21, 1938, Serial No. 247,098

14 Claims.

This invention relates to the conditioning of textile yarns and moreparticularly to the conditioning of filaments and yarns composed oforganic derivatives of cellulose such as cellulose acetate, cellulosepropionate, cellulose acetate propionate, and cellulose acetatebutyrate, to

- render them more amenable to textile operations such as knitting andthe like.

As is well known in the manufacture of yarns, particularly thosecomposed of or containing cellulose organic derivatives, it is necessaryto treat the yarn in order to reduce the tendency toward breakage of theindividual filaments or fibers when they are subjected to variousmechanical strains and to lubricate the yarn in order to facilitatehandling in such operations as spinning, twisting, winding and reeling.necessary to treat yarn to adapt it for use as warp or filling or forthe manufacture of various types of knitted fabrics. In knitting, it isparticularly important that the yarn be soft'and pliable in order thatit may conform readily to the contour of the needles and thus produce aclosely knit fabric free from such defects as stitch distortion, pinholes, laddering, and the like.

Heretofore it has been proposed to employ softening agents such aspolyhydric alcohols and similar agents as ingredients of yarnconditioning or lubricating formulas, generally inconnection withmineral, animal or vegetable oils. It has been found, however, that mostof the known softening agents and the various formulas.

containing them have certain drawbacks, one of the most serious of whichis high vapor pressure, and in some cases too drastic a solvent actionon the yarn. Many of such agents possess slight or insufiicient solventpower for the lubricants with which they are used, and it is accordinglynecessary to employ blending agents or emulsifying agents in order toobtain operable yarn treating formulas. In addition, many of the knownsoftening and lubricating agents are insufiiciently soluble in water topermit satisfactory removal by aqueous scour baths.

This invention has as its principal object to provide an entirely newclass of yarn conditioning agents which are particularly adapted for thetreatment of yarns composed of or containing organic derivatives ofcellulose and capable of lubricating, softening and rendering such yarnsmore amenable to kniting and other textile operations. A further andspecific object is to provide a class of conditioning agents whichaugment or assist the lubricating action of various 55 lubricants whenapplied to such yarns. A still It is also capable of employment in avariety of textile operations where complicated designs or stitches areemployed. Another object is to provide an improved type of yarn which isespecially amenable to textile operation including circular knitting,weaving, spinning and the like. Other objects will appear hereinafter.

These objects are accomplished by the following invention which, in itsbroader aspects, comprises the discovery that phosphated polyhydroxyalkoxyalkyl ethers and alkyl and aryl ethers of monoand poly-functionalalcohols having the following general formula:

z)t1n'CII C z--[ H2)il where Y is aphosphoric acid ester derivative,said ester being derived from the group of compounds consisting of thefree acid, its esters, and organic and inorganic salts, R isan alkylgroup, R R and R are organic radicals selected from the group consistingof the substituted and unsubstituted alkyl, aryl or heterocyclic groups,L is a mono-valent substituent selected from the group consisting ofhydrogen, hydroxy, acetal, ether, etc., and n is 0, 1, 2, etc., and b is0, l, 2, etc., may be used as yarn conditioning agents and particularlyas softening agents, with or without the addition of animal, mineral, orvegetable oils in the treatment of yarns composed of or containingorganic derivatives of cellulose. I have found that these compounds whenemployed as described in the detailed examples set forth below havea\slight solvent and/or softening action on cellulose organic derivativeyarns which renders such yarns soft and pliable without at the same"time having too drastic an action thereon.

Examples ofthe preparation of typical compounds of this typeare asfollows:

- PREPARATION OF COMPOUNDS Example 1 28.6 gm. of p-hydroxyethyl cetylether are dissolved in chloroform and treated with 16 gm. of phosphorusoxychloride in the cold and the reaction is completed by warming. Thechloride is hydrolyzed with aqueous sodium bicarbonate and the compoundobtained by concentrating the liquors. The disodium p-hydroxyethyl cetylether phosphate is water soluble. The product of reaction has theformula:

Example 2 One mole of CHz-O OieHu HOH CHPGHOH-CHaOH is reacted in amixture of dioxane and pyridine with one mole of (C16H33O)2POC1.

Example 3 One mole of OHa-O CuHn HOE ocm-cHoH-om-o our! is reacted aspreviously described with two moles of phosphorus oxychloride and thepotassium salt prepared.

Example 4 One equivalent of oleyl (OC2H4)n-OH is treated in a chloroformpyridine mixture with one equivalent of and the product worked up asdescribed in Example 1 so as to obtain a mono-potassium salt.

The reaction product has the formula:

25.2 gm. of HO-C2H4OC1oH2o -OC2H4OH are heated with gm. of phosphoricacid at 110-140 under reduced pressure for twenty hours. The phosphatethus obtained may be treated, if desired, with bases such as sodium,potassium or ammonium hydroxide; tetramethylammonium hydroxide, etc.,triethylamine, triethanolamine, dimethylcyclohexylamine, morpholine,ditetrahydrofurfurylamine, etc. to prepare mono or dibasic salts. Thereaction product has the formula:

no-mm-Omm-omm-o P-OZ Example 6 31.4 gm. of glyceryl mono-cetyl ether aredissolved in pyridine and treated with one equivalent of CmHa'P- fi iand the reaction is completed by warming. The

pyridine is removed under reduced pressure and the chloride ishydrolyzed. Any desired basic salt may be prepared. If desired, twophosphate groups may be introduced. The reaction product has theformula:

GET-(Khu na CHOH CHz-O P-O 015 31 Example 7 32.5 gm. of

(LE-0011K I CHiOH are treated in chloroform with 50 gm. of

012 Cl2|P-N and the reaction is carried out and worked up as previouslydescribed. The tetramethyl ammonium hydroxide or benzyl trimethylammonium hydroxide salt is prepared. The reaction product has theformula:

is dissolved in pyridine and treated with one or more equivalents of andthe product worked up to give an ethanolamine salt.

Example 10 28.8 gm. of

CH2CH2 era-00112 011 OH:

H-OCeHn 0 HIOH Example 18 A conditioning llq'uid particularly useful inthe preparation of cut staple fibers made of cellulose acetate and whichmaybe used for other textile operations is made up as follows:

- Parts Water soluble cellulose ether l CHr-O- P-ONa ONe Hr-O Naphthenyl1-10 Olive oil 98-89 Other examples of yarn conditioning compositionswhich may be applied to various types or yarns, particularly thosecomposed of or containing cellulose acetate, cellulose acetatepropionate,

cellulose acetate butyrate, and similar cellulose organic acid esters inaccordance with my invention and which render such yarns soft andpliable and especially well adapted for various textile operations,particularly knitting, are as follows:

Example 19 I Parts Blown olive oil.-." 69-80 Oleyl (O CIH4)1, r, ete.,P-ONa s OCH: 1-10 Tetrahydroiurluryl lactate Example 20 OHCyclohexylamine salt 2-5 H0 0113.0 omHn-0-0,H. 0-P

O OH Cyelohexylamine salt N cat's-foot oil 98-95 Example 21 CHr-O-CHQ OHOH H-O-Naphthenyl /0Na Iii-01" 0 Blown neats-loot oil 79-50Ethanolarnine propionate butyrate 20-30 Example 2 2 (HTetramethylammonium hydroxide salt CHz-O P LB: O H Tetramethylammoniumhydroxide salt... l-lO 6 Sperm oil Q 9990 Eaiample 23 PartsPentaerythritol triethyl ether diammonium phosphate. l-

Blown sperm oil $140 Sodium sulfate 2 S OH 'lriethanolaniine. l-lQ (n isl, 2, etc.)

Example 28 Fibers; threads, filaments, etc. composed of any textilematerial/in general or cellulose acetate in particular can be lubricatedfor various textile operations such as weaving, preparation of stapleyarns, thereto by means of a bath, suitable compound chosen from thegroup of compounds claims in this application, as for example: e

etc. by applying CnGar-O 01114-0 IklOH-NCHLOHM]: and

CHr-OOiaHu CH-OCnfiu HsO-P-OK I 0051111 Any of the above composition maybe applied to the yarn intended for use in circular knitting by means ofa bath, wick, spray, roller, pad or any suitable means. The amount ofconditioning liquid applied may vary between 5-25% by weight of theyarn. Usually, however, the amount of conditioning liquid applied isabout 10-15% by weight ofthe yarn. Yarn composed of cellulose acetateconditioned as described above gives excellent results when used in theetc. 0

circular knitting process.

As will be apparent from the above-examples and description theconditioning agents of 'my invention maybe applied by a. wide variety ofmethods. For example, I may employ the agent as an ingredient of thespinning dope from which the filaments are formed, the amount of theagent so employed depending upon a number of factors, tive' used inmaking the yarn, the solvent or solvent combination used in making upthe spinning solution, and the degree of softness or pliability desiredin the yarn, etc.

3 If the conditioning agent is to be applied to the 3 yarn afterspinning, this maybe done by bringing the yarn in contact with a wick,roll, or felt wet therewith, or the liquid may be applied by im-'merslon, spray, or otherwise. The particular point at which the liquidis applied may vary.

'It may, for example, be applied to the yarn inknitting, spinning,

wick, spray, etc. a

such as the particular cellulose derivaare dissolved in a mixture ofchloroform and pyridine and treated with 16 gm. of

OCH: II/ 01.?

N(CH:):

and the reaction is completed by warming. The reaction product has theformula:

CHQ.CHQ CHr-OCHr-(EH CH2 (gH-OCs'Hn O dm-or-oom 0 Mom Example 11 Oneequivalent of O-o-cmKooum-on is treated with one equivalent ofphosphorus pentasulfide in an oil bath at 50-150 until the reaction iscomplete. The product is treated with water and neutralized withmorpholine. The reaction product has the formula:

C ll,

Example 12 One equivalent of the reaction product fromtetrahydrofurfuryl alcohol and ethylene oxide is treated in boilingchloroform with phosphorus pentoxide. The reaction product is treatedwith 33.4 gm. of m-hydroxy cetyl phenyl ether are dissolved in a mixtureof chloroform and pyridine and treated with 16 gm. of phosphorusoxychloride. The reaction product is worked up as previously describedand any desired salt such as the triethylamine, benzltrimethylammoniumhydroxide, etc. prepared. The reaction produce has the formula:

In a similar manner we may react:

is dissolved in a mixture of dioxan and pyridine and reacted with onemole of POC13. The trimethylbenzylammonium hydroxide salt is prepared.

Example 15 2 pounds of 1-methylamine-4-ethy1aminoanwith one pound of andpoured into 200 gallons of water, then heated to 60-85. 100 pounds ofcellulose acetate in the form of taffeta, crepe fabrics, etc. areentered and dyed a deep blue shade. Softwater is not necessary with adispersing agent of this type.

In accordance with the invention these compounds may be applied directlyto the yarn during or after spinning. or may be added to the spinningsolution itself. I have found that these compounds have exceptionalsolvent powers which enable them to dissolve mineral oils and blown andunblown, drying and semi-drying, vegetable and animal oils andaccordingly they may be, and preferably are, employed as ingredients ofyarn conditioning or lubricating formulas in conjunction with agentswhich function wholly or partially as lubricants.

In the following examples and description I have set forth several ofthe preferred embodiments of my invention, but they are included merelyfor purposes of illustration and not as a limitation thereof.

My invention will be more readily understood by reference to thefollowing examples in which typical applications of the invention areset forth.

Example 16 UIIOH Dimethylcyclohexylamine salt is applied to textilematerials (silk, wool, cotton, viscose, cellulose acetate,'etc.) bymeans of a bath, wick, spray, roller, etc., to facilitate theirknitting, weaving, spinning etc. Yarns lubricated with the above type oflubricant are of special value in the preparation of cut staple fibers.These fibers may be oiled before or after cutting.

Example 17 A conditioning liquid is made up as follows:

Parts by weight l\ 4) 0H Diethyl cyclo hexylamine salt Wafer and appliedto textile materials such as silk, wool, viscose, cotton, celluloseacetate, etc., as in Example 16. .If the yarn is intended primarily forknitting the amount of conditioning liquid applied may vary from 4-25%by weight of the yarn and if for weaving between 1-5% by weight.Cellulose acetate filaments treated as described are quite soft andpliable and give improved results in various textile operations such asweaving, knitting etc., and especially in the preparation of cut staplefibers.

Other examples of suitable lubricating mixtures having anti-staticproperties which are used as described in Examples 16 and 17 follow.

ple fiber manufacture, the liquid may be applied to the yarn prior to,or after cutting into staple lengths.

The amount of the agent so employed will vary widely depending upon theresults desired, the specific nature of the material to which the agentis applied, the use to which the yarn is eventually to be put and otherfactors. For example, in a given case where a cellulose organic acidester yarn such as a yarn composed of cellulose acetate, is intended forknitting, about 4 to 25% or more by weight, based on the weight of thedry yarn, may be satisfactory, while if the yarn is intended forweaving, the amount may vary between about 1 and 5%.

Although in the above examples I have referred primarily to yarntreating compositions containing only the conditioning agent and an oil,other ingredients such as solvents, nonsolvents, emulsifying agents,blending agents and the like, may be added within the scope of myinvention. Likewise, various dyes or other coloring matter may beincluded in case it is desired to permanently or fu'gitively tint or dyethe ma-v terial undergoing treatment.

Although I have found it convenient to illustrate my invention byreference to compositions containing specific percentages of the variousingredients, these percentages may vary widely depending upon theparticular purpose for which .the composition is intended. For example,if it is desired to control the solvent or softening action of theconditioning agent the amount of the agent may be adjusted as, forexample, by reducing the amount of the agent and correspondinglyincreasing the amount of oil or other inredient.

While I have described my invention with particular reference to thetreatment of yarns composed of organic derivatives of cellulose such ascellulose acetate, the conditioning agents and formulas described hereinare applicable to the tor, neats-foot, sperm and other oils.

conditioning of many other types of cellulose derivative yarns such asthose composed of or containing cellulose propionate, cellulosebutyrate, cellulose acetate propionate, cellulose acetate butyrate,ethyl cellulose, methyl cellulose, benzyl cellulose and others as wellas to the conditioning of silk, wool, cotton, viscose and other naturalor artificial materials.

The term yarn as used herein and in the claims is to be understood asincluding a single filament, a plurality of filaments associated intothe form of a thread, either of high or low twist, single or multiplethreads associated or twisted together, composite threads composed of amixture of natural and artificial filaments or a composite thread formedby twisting together individual strands of natural or artificialmaterials, as well as cut staple fibers produced from natural and/orartificial filaments or threads and spun yarn produced from such staplefibers.

As indicated above; the yarn conditioning agents of my invention areexceptionally good solvents for a wide variety of mineral, blown andunblown, drying and semi-drying animal and vegetable oils such ascottonseed, olive, cas- This enables them to be used with any of suchoils in making up a variety of yarn treating formulas of varyingcomposition.

The yarn conditioning method and compositions of my invention possessmany outstanding advantages. The fundamental and outstandingcharacteristic of the agents employed in accord ance with the inventionis their ability to soften yarns, especially those composed of orcontaining organic derivatives of cellulose such as cellulose acetateand render them soft and pliable and amenable to various textileoperations, especially operations such as those involved in weaving andknitting where complicated designs or stitches are employed, without toodrastic an action on the yarn material. Another outstandingcharacteristic of these compounds is their exceptional solvent power fora Wide variety of mineral, animal, and vegetable oils and their abilityto act as lubricating assistants in conjunction with these oils whenapplied to such yarns. In addition, due to their solubility in water,they may be readily removed from yarns and fabrics bymeans of the usualaqueous scour baths. By employing the yarn conditioning agents andmethod of my invention as herein described, one is enabled to obtainhighly satisfactory results in the manufacture of yarns and wovenfabrics and especially the production from these yarns of closely knitfabrics free from defects such as pin holes, stitch distortion,laddering and the like.

What I claim is:

1. The process of conditioning yarn to render it more amenable totextile operations including knitting, weaving, spinning and the like,which comprises applying thereto a lubricating and softening compositioncontaining as its essential lubricating and softening component an etherselected from the group consisting of the phosf phated polyhydroxyalkoxyalkyl ethers, and alkyl and aryl ethers of monoand poly-functionalalcohols.

2. The process of conditioning yarn composed of or containing organicderivatives of cellulose to render it more amenable to textileoperations including knitting, weaving, spinning and the like, whichcomprises applying thereto a lubricating and softening compositioncontaining as its essential lubricating and softening component an etherselected from the group consisting of the phosphated polyhydroxyalkoxyalkyl ethers, and alkyl and aryl ethers of monoand polyfunctionalalcohols.

3. The process of conditioning yarn composed of or containing celluloseacetate to render it more amenable to textile operations includingknitting, weaving, spinning, and the like, which,

comprises applying thereto a lubricating and softening compositioncontaining as its essential lubricating and softening component an etherselected from the group consisting of the phosphated polyhydroxyalkoxyalkyl ethers, and alkyl and aryl ethers of monoand poly-functionalalcohols.

4. The process of conditioning yarn composed. of or containing celluloseacetate to render it more amenable to textile operations includingknitting, weaving, spinning, and the like, which comprises applyingthereto a lubricating and softening composition containing as itsessential lubricating and softening component an ether selected from thegroup consisting of the phosphated poly-hydroxy alkoxyalkyl ethers, andalkyl and aryl ethers of monoand poly-functional alcohols, and a textilelubricant.

5. The process of conditioning yarn composed of or containing celluloseacetate to render it more amenable to textile operations includingknitting, weaving, spinning, and the like, which comprises applyingthereto a lubricating and softening composition containing as itsessential lubricating and softening component glycerol dioleylether-phosphate diethyl cyclohexylamine salt.

6. The process of conditioning yarn composed of or containing celluloseacetate to render it more amenable to textile operations includingknitting, weaving, spinning, and the like, which comprises applyingthereto a lubricating and softening composition containing as itsessential lubricating and softening component disodium thio-phosphate ofethylene glycol naphthenyl ether.

'7. The process of conditioning yarn composed of or containing celluloseacetate to render it more amenable to textile operations includingknitting, Weaving, spinning, and the like, which comprises applyingthereto a lubricating and softening composition containing as itsessential lubricating and softening component pentaerythritol triethylether phosphate diammonium salt.

8. A conditioning agent for rendering textile yarns composed of orcontaining organic derivatives of cellulose more amenable to textileoperations including knitting, weaving, spinning, and the like, whichcomprises an ether selected from the group consisting of the phosphatedpolyhydroxy alkoxyalkyl ethers, and alkyl and aryl ethers of monoandpoly-functional alcohols, and a textile lubricant.

9. Textile yarns amenable to textile operations including knitting,weaving, spinning, and the like, impregnated with a lubricant containingas 40 its essential lubricating and softening component an etherselected from the group consisting of the phosphated polyhydroxyalkoxyalkyl ethers, and aIkyIKand aryl ethers of monoand polyfunctionalalcohols.

10.,TeXtile yarns composed of or containing organic derivatives ofcellulose amenable to textile operations including knitting, weaving,spinning, and the like impregnated with a conditioning agent comprisingan ether selected from the group consisting of the phosphatedpolyhydroxy alkoxyalkyl ethers, andalkyl and aryl ethers of monoandpoly-functional alcohols.

11. Textile yarns composed of or containing organic derivatives ofcellulose amenable to textile operations including knitting, weaving,spinning, and the like, impregnated with a conditioning agent comprisingan ether selected from the group consisting of the phosphatedpolyhydroxy alkoxyalkyl ethers, and alkyl and aryl ethers of monoand.poly-functional alcohols, and a textile lubricant.

12. Textile yarns composed of or containing cellulose acetate amenabletotextile operations including knitting, weaving, spinning, and thelike, impregnated with a lubricant comprising glycerol dioleylether-phosphate diethyl cyclohexylamine salt.

13. Textile yarns composed of or containing cellulose acetate amenableto textile operations including knitting, weaving, spinning, and thelike, impregnated with a lubricant comprising disodium thio-phosphate ofethylene glycol naphthenyl ether.

14. Textile yarns composed of or containing cellulose acetate amenableto textile operations including knitting,'weaving, spinning, and thelike, impregnated with a lubricant comprising pentaerythritol triethylether phosphate diammonium' salt.

JOSEPH B. DICKEY.

